Alkyl-isopropylene-phenols and process of making same



Patented July 28, 1931 Q UNITED STATES PATENT KAHLBAUM AKTIENGESELLSCHAFT; or BERLIN, GERMANY" ALKYLISOPROPYLENE-PHENOLS AND PROCESS OF MAKING SAlN IE No Drawing. Application filed June 20, 1927, Serial No;200;290, and in Germany-June 29, 1926.

My invention refers to chemical products having valuable properties as starting mate rials for the manufacture of odorants and disinfectants, such products being obtained 5 by decomposition of the products resulting in the condensation occurring at a temperature slightly above room temperature in the presence of gaseous hydrochloric acid between alkyl phenols and ketones as described in my copending application for patent of the United States filed of even date herewith Ser. No. 200,289 and entitled Chemical products and process of making same. These products of condensation contain acythe constitution shown, for the product from m-cresol and acetone, by the following formula I have now ascertained that if these products are heated to 800 0., the components distill over in a quantitative manner and'can be separated by fractional distillation. I prefer expediting the distilling of the components from the material heated to about 300 C. by slight evacuation, the degree of evacuation being chosen in such manner that the original product does not distill over.

Example 1.-The product of condensation from m-cresol and acetone described in my copending application above mentioned, if heated to about 300 C. is decomposed into its constituents, Which distil over. From the distillate can be separatedby fractional distillation the valuable compound 3-methyl-6- isopropylene phenol having the formula e 0 orn 0 lisable hydroxyl groups and probably have Example 2-.The productof condensation from p-cresol and acetone describedin my I copendingapplication'is heated to 300310 (3., as described With reference to Example 1, and the components are distilled over. There is obtained by fractional distillationthe con'r'-- e pound 4 methyl-6-isopropylen'e phenol hav'-' ing the formula and boiling at 213-218 C.

Example 3.The product of condensation from crude cresol', being a'mixtureof n1- and pcresol-, and acetone, described in" my 00'- pendingapplication, is heated to about 300 0., When its constituents Willdistil over and can be sep arat'edbyfraction'al distillation, resulting in the recovery of 3-rnethyl-6-isopropylene phenol and l methyl-G-isopropylene phenol, which appearto be constituted according to the formula e I CH3,

, O Y I V i CH2 cm on CH C 1..

on v

and, boili g at213-218CL GH O OHa O V V foo to effect decomposition, subjecting the products of decomposition to fractional distillation and collecting the fraction conta ning the methyl-isopropyleiiephenols.

2. The process of producing methylisopropylenephenols comprising heating to about 300 C. compounds resulting "from the condensation, occurring at a ten'ipei'ature slightly above room temperature in the presence of gaseous lrvdrochioric acid of crude cresol and acetone, the product being a mixture of compounds having the formulae:

OH C/CH3 CH-3\ CU3\C/C1I3 on -on and on OH/ om I on/ oin to effect decomposition, subjecting the prodnets of decompositimi to *tionai distillatlon and collecting 1 containing one tract the methyl-isopropylenephenois.

3. The process of pro hig niethylisopropylenephenols compr in heating in vacuo to about 300 C. con ,ounds resulting from the condensation OCCU ring: at a temperature slightly above room temperature in the presence of gaseous hydrochloric acid of a cresol and acetone and which have the formula:

to effect decomposition, subjecting the products of decomposition to fractional illation and collecting the fraction containing the methyl-isopropylenephenols.

4. As a new product the product obtainable by fractional distillation at about 300 C. of a mixture of compounds having the formulae:

on, H

| C \O/CH, CH: CH3 O/CHs on on and 0 cm 011/ OHQ H 0113 oin supposed to be a mixture of 3methy1-6-isopropylenephenol and i-methyl-6-isopropylenephenol.

In testimony whereof I ailix my signature.

HANS JORDAN. 

